Methyl salicylate (2-hydroxybenzoic acid methyl ester) is a commonly used flavorant. It is the major constituent of wintergreen oil which can be obtained by steam destillation from parts of the plant, typically the leaves. Methyl salicylate is also produced by esterification of salicylic acid with methanol.
The sensory properties (odor and taste) of methyl salicylate are described as warm, sweet, phenolic, wintergreen.
Methyl salicylate is a commonly used flavor and fragrance compound which provides the sensory properties of wintergreen. It is used in perfumes, foods, beverages, candies, chewing gums, oral care products and so forth. It is also used to enhance the flavor of mint flavored products, for example, those flavored primarily with peppermint or spearmint oils.
Methyl salicylate is also used as an active ingredient in topically applied anesthetic ointments promoted for relief of muscle aches, arthritis and similar complaints. Salicylic acid derivatives, most notably acetyl salicylic acid (more commonly known as aspirin), often have pharmaceutical properties such as anagestic, anticoagulant, antipyretic and anti-fungal activity. Not surprisingly, these pharmaceutical agents are generally toxic to some degree. Methyl salicylate itself is known to be toxic above certain dosage levels.
While products flavored with methyl salicylate have gained widespread consumer acceptance, the use of such a compound with pharmaceutical properties and a degree of toxicity poses a potential risk of adverse publicity or governmental regulation which could limit the level at which it may be used, or prohibit it entirely.
Furthermore methyl salicylate is not stable in alkaline media. This instability in alkaline media limits the number and type of compositions and products into which methyl salicylate may successfully be incorporated.
The availability of a replacement compound for methyl salicylate would be highly desirable.
U.S. Pat. No. 5,795,616 relates to the use of 2′-hydroxypropiophenone as a flavor ingredient. More particularly it relates to the use of 2′-hydroxypropiophenone as an enhancer, or as complete or partial replacer for methyl salicylate in chewing gum, foods, dentrifices, mouthwashes and other orally consumable compositions. Although this document describes the use of 2′-hydroxypropiophenone as a flavor and as a replacer for methyl salicylate, the best results are obtained when using a mixture of 2′-hydroxypropiophenone and methyl salicylate. The preferred replacement level of methyl salicylate is about 10 to 50% by weight.
WO 01/68044 describes oral compositions comprising a wintergreen flavor imparting ingredient and having an alkaline pH, wherein the wintergreen flavor imparting ingredient is 2′-hydroxypropiophenone.
Until now, it is believed that no satisfactory, non-salicylate substitute for methyl salicylate in fragrance and/or flavoring compositions has been proposed.